Olivia

Olivia Wilde was babysat by Christopher Hitchens. Richard Holbrooke and Peter Jennings were family friends. She is married to Italian royalty and has been known to take phone calls from Barack Obama. And the star of House’ also happens to look, well, like THIS. So how’s a girl like her supposed to survive a career in Hollywood?

Olivia Wilde and i are going drinking. Yeah, that’s my plan. We’re going to the grungiest, scuzziest sticky-floor dive we can find, and we’re going to start with shots of Jäger, followed by tequila, some Jack, and three fingers of scotch. We’re going to shoot sloppy pool and play Galaga and persuade two burly Hells Angels on their Harleys to drive us to an In-N-Out Burger, where I’ll order the Double-Double and Olivia, a vegetarian, will have a veggie burger and maybe a few fries, because, you know, she’s drunk, and those fries are amazing. Then we’ll climb into the hills and scale the famous hollywood sign, where we’ll sit until sunrise on opposite sides of the giant H, and Olivia will grandly recall her adventures in show business before she throws up, as I hold her flowing brown hair.

Reality: Olivia Wilde and I are going to a…wine bar. This is the plan I received via e-mail a few hours ago. A wine bar called the Otheroom on bougie-crunchy Abbot Kinney Boulevard in Venice, California, not far from the famous boardwalk with the perma-tanned Rollerbladers and the medical-marijuana club that slowly scoops cannabis gelato. When I walk in, Wilde is sitting alone at a window table with a glass of Austrian white and Jitterbug Perfume, a Tom Robbins paperback. I go to the bar, choke, and order a rosé. I may as well order an ascot and a dress. There will be no Hells Angels Harley rides tonight.

But it’s fine, it’s cool, it’s great. This is Wilde’s town, her home court, her vibe. A self-confessed hippie, she lives not far from here, in a renovated concrete-and-steel loft, with a pair of dogs named Paco and Lola. Unpretentious Venice is pretty much the only city she’s lived in since moving from Washington, D.C., seven years ago, an 18-year-old prepster delaying her freshman year at college for a shot at Hollywood. It’s not a place for showbiz jackholes, which is one of the reasons Wilde adores it. It is not where you come to get photographed in your Juicy sweats and Gucci shades ambling out of Pinkberry frozen yogurt. In Venice, they protested the Pinkberry’s opening.

“For me, Venice just feels the most like the East Coast,” Wilde says. She is wearing a black dress with a white-and-purple scarf, and her cascading hair, sometimes dark, sometimes blond, is reddish brown. Her eyes are sharply green; there’s a tiny scar on her right cheek, from scratching herself when she was one day old. “It’s pedestrian-ruled and has a neighborhood vibe I didn’t experience anywhere in Los Angeles. A lot of architects live here, and more actors, too—which I’ve noticed partly because of the increasing presence of the paparazzi, which feels so weird to me.” She takes another sip of white wine. “It just feels like Venice should be off-limits.”

Wilde, 25, is not at the point where the paparazzi chase her into vintage-clothing stores and prowl for her burrito wrappers in the trash. But there’s a sense that her moment, if not imminent, is coming. “From minute one, I thought, That girl is going to be a huge star,” says the producer Josh Schwartz, who gave Wilde her first major break, casting her as Mischa Barton’s bisexual love interest in the teen soap The OC. Justin Timberlake, who starred opposite Wilde in the 2006 true-life caper Alpha Dog, raves that she “has all the qualities of an actress who’s going to have a long career.” Hugh Laurie, the star of the misanthropic medical drama House—on which Wilde now plays a key role as a mysterious young doctor named Thirteen—is equally charmed. “Right from the first day, Olivia was pretty hard to ignore,” Laurie says.

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Next year Wilde’s stature will rise to new heights with her role opposite Jeff Bridges in Tron: Legacy, a “reimagining” of the cultishly popular 1982 video-game movie. Tron: Legacy isn’t due until 2010, but the project hijacked this year’s Comic-Con in San Diego with a few minutes of moodily electrifying footage.

“I’m definitely at this point now where things are shifting, they’re changing very fast,” Wilde says cautiously, as a shifty guy nearby checks his iPhone e-mail or sends a snapshot to Perez Hilton. “The only role I really don’t understand is this recent sort of ‘sexiest-vin’ thing. It doesn’t feel like me, doesn’t feel natural.”

Yes: the sexiest-vin thing. Not long ago, the actress Megan Fox gushed that Wilde was so sexy it made her “want to strangle a mountain ox,” and given Fox’s own babe-osity, the effect was not unlike having Oprah plotz over a debut novel. Soon after, Wilde was ranked number one in Maxim’s Hot 100 list of the most beautiful women in the world, an honor that flattered but made her reach for the stemware. “The day they announced it, I hid in my bathtub with a big glass of wine,” she says. “Anytime anyone describes you with a superlative, people are going to disagree. And I didn’t want to have to deal with those people.”

Wilde, of course, is not the first young actress to feel awkward in the face of babedom. It’s not as if she isn’t an active co-conspirator—I mean, hello, photo to your right. Babedom can help. But there’s always the risk of it becoming who she is and overshadowing the rest, like the part that canvassed door-to-door for Barack Obama, fund-raises for the ACLU, and can be found reading 600-page books on Iraq.

I fetch Wilde another glass of Austrian white from the bar. When I sit down, she talks about seeing Robert Pattinson, the raffish Twilight phenom, being mobbed at this year’s Comic-Con. “I did not envy him. I think it’s the frog-in-boiling-water concept,” she says, referring to the fable about the amphibian that is slowly cooked to death without realizing it. “Robert Pattinson jumped in boiling water and has stayed in it, and hopefully will survive. Whereas I entered the water when it was cold, and it’s been slowly heating up—a slooooow boil.” Wilde pauses. “Maybe I won’t realize when it’s getting dangerous.”

Olivia Wilde is married, and has been for six years. It’s a personal detail she’s been advised to downplay, not to elaborate upon in public, surely because of its fantasy-depleting tendencies. For a young actress, it’s more socially permissible to be a cokehead nightmare than a satisfied domestic. “There were times when people thought it would really hurt me,” Wilde says, rolling her eyes. “People said I shouldn’t be married, or lie about being married, or I should be married to a movie star or rock star.”

Wilde’s husband is Tao Ruspoli, a wavy-haired 33-year-old filmmaker and flamenco guitarist whom Wilde met not long after moving to L.A. After a whirlwind courtship, the couple eloped, getting married on a funkily painted school bus with only a pair of witnesses. “They’re like Barack and Michelle,” says Wilde’s friend, actress Megalyn Echikunwoke. “It’s like, give me a break—could you be any cuter? They’re probably going to have perfectly amazing babies, and they’ll be even more annoying.”

Nearly every story about Wilde to date makes mention of Ruspoli’s aristocratic lineage—he’s the son of an Italian prince, the late Roman bon vivant Dado Ruspoli, which technically makes Wilde an Italian princess. “Dado was friends with the Stones, with Salvador Dalí, orgies with Brando, all these people,“ Wilde says. “We have pictures of him bathing Brigitte Bardot.“ Tao’s family was also tormented by drug use—his father, mother, and brother all struggled with opiate addiction—which inspired Fix, an indie movie arriving this November written and directed by Ruspoli in which Wilde stars as a young woman reluctantly transporting her boyfriend’s brother to rehab. “Olivia and I joke that we took the plunge of getting married after six months, but it took us four years to make a movie together,“ says Ruspoli. “It was a much more dangerous commitment.“

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Wilde’s own family is hardly conventional. Her parents, Andrew and Leslie Cockburn, are both longtime investigative journalists based in Washington, D.C. Andrew is the author of unfrivolous books like The Threat: Inside the Soviet Military Regime and Rumsfeld: His Rise, Fall and Catastrophic Legacy. Leslie, meanwhile, has produced or directed segments for 60 Minutes, ABC News, and Frontline. This fall the couple will release a documentary about the housing crisis called American Casino.

When they weren’t traveling on assignment to places like Afghanistan, Colombia, and Iraq, Wilde’s parents were legendary for dinner parties at their rambling Georgetown town house. Andrew and Leslie Cockburn remain fixtures on the D.C. social circuit; over the years, journalists like Seymour Hersh and the late Peter Jennings have been friends.

“Olivia was exposed to a lot of very clever people when she was little,” Leslie Cockburn says. She recalls Olivia eavesdropping one night on a conversation between Richard Holbrooke and Mick Jagger—until the Rolling Stone turned around and shooed Olivia to bed. “How many girls were told to go to bed by Mick Jagger?” she asks.

Back inside the bar, Wilde—who took Oscar Wilde’s last name upon launching her acting career—vividly recounts hiding under the table during dinners and letting the wine-soaked debates wash over her. “I’d fall asleep listening long before I understood what they were talking about,” she says. “I appreciated the constant excitement, the murmur of all these engaged conversations. Christopher Hitchens used to babysit me when I was young.”

“With Olivia you could tell it was going to be the movies or stage or TV or nothing,” says Hitchens, the noted writer and political raconteur who briefly lived with the Cockburns and describes it as the type of place where the worn memoirs of the French military leader Ferdinand Foch were used to prop up a window. “Olivia sort of lived the part—very pretty, and, well, the Victorian term for it is headstrong. She wasn’t going to be overlooked or ignored.”

Accepted by Bard College in upstate New York, Wilde begged to take a year off to try Hollywood. Her parents agreed, but on the condition that she take a job with a casting director who was a family friend. “That [job] was really the best thing I could have done, because I was in the belly of the beast, witnessing what would torture me for the rest of my life,” Wilde says. “You’re sorting through thousands of head shots—it’s a reality check.”

Still, Wilde got unusually lucky. After losing out to Mischa Barton for the lead role in The OC, she landed a featured part in Skin, a skeevyish Jerry Bruckheimer series for Fox about a pair of entangled families, one led by a prosecutor, another by a pornographer. Wilde suddenly found herself jetted to press junkets and handed front-row seats at the World Series, but the show was quickly canceled. “One minute there were posters of her forty-feet high over Sunset Boulevard, and the next they were gone—bang!” says Andrew Cockburn.

Undeterred by her misadventures in Skin, she plunged into new projects: The Black Donnellys, another short-lived TV series; Alpha Dog; and a grisly slasher movie called Turistas, about a group of unnaturally pretty kids who get their organs harvested on a Brazilian beach holiday. Her heady family rolled with her blooming career. “They’d support anything I’d do,” she says. “They saw _Turistas _and were like, ‘It really is an important film!’ ”

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Her most attention-grabbing role during this period would instead be a thirteen-episode run on _The OC _as Alex Kelly, who shared a rendezvous with Adam Brody’s Seth Cohen and a then shocking and now legendary kiss with Barton’s Marissa Cooper. “Olivia was totally game,” says Josh Schwartz. “I wanted to keep her on the show.” Schwartz says that the network and advertisers were made “very nervous” by Alex Kelly’s bi-curious story line. “They kind of made us write her out,” he says regretfully.

Now Wilde is playing another bisexual character on television—Thirteen, a.k.a. Dr. Remy Hadley, the enigmatic young M.D. on House who sufferers from Huntington’s disease and occasionally displays a Kate Moss–style self-destructive streak. Wilde is irked by suggestions that she’s playing another bi-cur ratings magnet—“I sort of resent people pigeonholing Thirteen as the sexy gay doctor”—but she knows labels are tough to shake in Hollywood. The town is rough on its young actresses today. It’s hard not to notice Wilde’s ascension against the troubles of Mischa Barton, now getting chewed up regularly in tabloids.

Oddly, it may be the one anomaly in Wilde’s life—her young marriage—that gives her ballast. “I don’t want to make assumptions about Olivia’s relationship, but I can only imagine that it’s a big part of her grounded nature,” Timberlake says earnestly. “Anytime you have someone you love, companionship, it’s good. I admire her.”

Barack Obama has called olivia wilde. Of course he has. Along with her then House co-star Kal Penn, Wilde signed on early to the Obama steamroller, campaigning for the Illinois senator in Iowa and New Hampshire, as well as in Shreveport, Louisiana, last summer during the filming of Harold Ramis’s Year One. “She’d be out canvassing alone in some of the roughest neighborhoods in Shreveport,” says Ramis. “Very brave.”

One afternoon on the set of House, Wilde’s cell phone began ringing. The future president was on the line, calling to thank Wilde for her campaign service. The conversation was brief and cordial. Then Wilde hung up and began to jump and scream like a Jonas Brothers fan: “I was just squealing and squawking, trying to replay the whole thing.”

But Wilde hadn’t actually hung up her phone. Through a friend, she learned that Obama was still on the line and heard every shrill decibel of Wilde’s fangirl outburst, laughing the entire time at the lunatic on the other end. “It was awful—horrifying!” Wilde says. “But apparently he was flattered.”

It’s the day after our wine-bar summit, and I’m sitting with Wilde at Intelligentsia, a Jedi-level coffee shop not far down the road on Abbot Kinney. If you dig highbrow artisanal joe, you’ll thrill to Intelligentsia’s vest-wearing beanologists with their Wonka-esque beakers and temperature gauges. If you dig Dunkin’ Donuts, you’ll just laugh. Wilde is sitting on a concrete block behind the “slow coffee” station, dressed in a yellow shirt and jeans. For the first time in our visits, someone asks for an autograph. “You’re great,” the fan says, before disappearing back to her caffeine.

Wilde’s still getting used to this. Fame is still sparkly and unscary; she can mostly move without interruption. But those closest to Wilde have been preparing for a long time. “It’s slightly weird, and I know it’s only going to get weirder,” her sister, Chloe, says. “I think she’s amazing how she deals with it.”

Wilde is determined not to become the frog in the boiling water. Nothing about her manner suggests a derailment is coming, but Wilde confesses she’s turned to a new spiritual adviser: family friend Julie Christie, the British actress who defined a generation of female glamour. As Wilde navigates a similar juncture, Christie has given wise counsel.

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“She said that none of this really matters,” Wilde says. “It’s all temporary. She got certain opportunities because she was a beauty, a fashion icon, and she was very grateful for them. And that’s the stance I’ve taken—I’m very grateful, very flattered, and if it gives me an opportunity to work, great. It’s not something I denounce or resent.”

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